He has appeared in diverse roles since his first lead role in 1999′s October Sky, followed by the 2001 indie cult hit Donnie Darko, in which he played a psychologically troubled teen and onscreen brother to his real-life sister, actress Maggie Gyllenhaal. The same year, he garnered critical acclaim and an Academy Award nomination for Best Supporting Actor as Jack Twist in the film Brokeback Mountain opposite Heath Ledger. As an 11-year-old he made his acting debut as Billy Crystal’s son in the 1991 comedy film City Slickers. The film earned $32 million and was described in the Sacramento News and Review as Gyllenhaal’s “breakout performance.” Donnie Darko, Gyllenhaal’s second major film, was not a box office success upon its initial 2001 release, but eventually became a cult favorite. His performance was described by one critic as “silly, cliched and straight to video.” Gyllenhaal had more success starring opposite Jennifer Aniston in The Good Girl, which premiered at the 2002 Sundance Film Festival; he also starred in Lovely & Amazing with Catherine Keener. in both films he plays an unstable character who begins a reckless affair with an older woman.

Jake Gyllenhaal Eats Worms Jake Gyllenhaal proved he is not afraid of a meaty challenge on survival expert Bear Grylls’ upcoming TV special by eating a worm on camera.  … [link]